The top 3 pain points every founder experiences… and what to do about them

Brent Lowe
5 min readApr 26, 2022


Scaling a business isn’t always fun. Sometimes it’s downright painful. Struggling founders wonder, “Do all founders feel like this? What am I doing wrong? What should I be doing differently?”

At the beginning of the scaling journey, the “people stuff” isn’t urgent. The team is small. Communication flows and the growth trajectory provides energy.

Before you know it, you cross a line. Maybe it’s when the team hits 10 people or 12 or 15. Complexity creeps in. Tensions rise. A deep-seated feeling of angst surfaces. Things feel off balance.

I’ve had plenty of closed door conversations with founders over the years as they face the challenges of growth. While circumstances vary, their pain points boil down to the same three things every time. Burnout, chaos and doubt. Here’s what that feels like, and how to find a path forward.


When a company starts with one or two or three people, founders do everything. You’re growing a business with too much to do and not enough hands to help. Stuff falls off the edges of your plate. As the business grows, the problem compounds. You feel the need to keep every ball in the air. You don’t have the money to hire in people with the required expertise so you hire in people with good enough experience. Cue the pain. While trying to do too much yourself, you also need to coach the team. With no light at the end of the tunnel, you flirt with complete and utter burnout.

Moving forward from overwhelm and burnout

When we’re anxious, our brains don’t function optimally. It’s biology. Having loops of overwhelm stuck in your head becomes debilitating. You need fresh perspectives and new ideas. Your brain is no longer able to provide those things to you. It’s not unusual for me to get to the end of a coaching call and have my client say, “I feel so much better now that we’ve talked things through.” That’s because we’ve been able to break down the overwhelm and do some fresh solutioning on a point-by-point basis. Having a safe place to go to unpack the overwhelm is a necessity. It’s not until we have some way to break that cycle that we can move forward. Who can help do that for you?


Chaos in a scaling business is the perpetual feeling that the wheels are falling off the bus. When the team consists of a handful of people, it’s easier to stay on course. Daily (or hourly) conversations can keep you on track. But what about when your team hits double digits and people are off doing their own thing? Are they doing the right thing? Is everyone connected and aligned?

When you reach burnout and layer on the “people stuff,” the result is chaos. Simple questions like, “What meetings should we be having?” and “Who’s going to do what?” cause stress to an already overtaxed system. Why? Because there is no solid foundation to support the team.

Moving beyond chaos as you scale your business

Our team at BASE Associates does an immense amount of foundation-building when working with early-stage scaling companies. The focus is on finding simple, easy-to-implement prototypes that reduce chaos. We start small and iterate, introducing complexity only when absolutely necessary. We try an experiment for a few weeks and see what happens, then iterate if needed. Here’s the simple model we follow over and over again.

First, we identify a specific tension or concern or challenge. Next, we talk to the team to understand their beliefs and philosophies about how problems like this get solved. We share our own experiences too.

We take the resulting philosophy and figure out the simplest, easiest set of practices (meetings, checklists, questions, roles, processes, etc.) that can bring that philosophy to life. To ensure the practice gets some momentum, we look for ways to turn it into a routine. We then decide who needs to be in the know and onboard those people to the plan.

Lastly, we schedule a retrospective a few weeks or months into the future to see how our experiment worked. With a bit of practice these six steps can be completed in minutes. What tension can you use to experiment? If you need some help, send me your challenge I’ll share some ideas with you.


Ever feel like everybody but you have got it all figured out? Usually the voice in our heads repeats (at nauseam) some version of: “I’m not good enough.” “I’m going to fail.” “I can’t do this.” “I’m not as good as [insert name here].” Despite a reputation of being ambitious risk-takers, every founder has underlying doubts about their personal ability to do the job. When your team grows, the fear of failure grows with it. You feel the need to show strength, be a mentor and have it all together. So, what do you do when doubt becomes a monster in your head?

Overcoming doubt when scaling your business

Doubt is one of those things that us humans — especially founders — don’t like to share openly. Having a safe space where you can express and test your doubt is essential. Those conversations help to separate valid concerns from the unhelpful (and usually untrue) internal talk tracks clouding your judgement — judgment of your competence and your overall performance. Who can be that mentor for you? Consider joining a CEO group or starting your own.

In Part 2 of this blog series I share our 5C model for Scaling Together along with a free assessment you can take to test your readiness to scale.

I help Founder CEOs of companies between 5 & 40 people who are experiencing early stage success and are ready to scale — especially those wanting to build shared responsibility and accountability within their team. Click here to get your free copy of the 5 principles and 6 leadership roles for scaling a sustainable, prosperous company.



Brent Lowe

The Scale Coach for Founder CEOs and co-author of Lead Together: The bold, brave, intentional path to scaling your business